1,2-Dimethoxyethane → 2-(1,3-Dioxaindan-5-yl)acetaldehyde

HRID 1657876Notes

Reaction equation

HRID 1657876 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH:11](S(C)=O)SC)=[CH:4][C:3]=2[O:2]1.C[O:18]CCOC>>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH:11]=[O:18])=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 21530764Methyl 2-(3,4-methylenedioxyphenyl)-1-methylthioethyl sulfoxide

Product 1

HCID 2678892-(1,3-Dioxaindan-5-yl)acetaldehydeYield 45%

Procedure

2.08 g of methyl 2-(3,4-methylenedioxyphenyl)-1-methylthioethyl sulfoxide was dissolved in 20 ml. of 1,2-dimethoxyethane, and with the addition of 1.71 g of cupric chloride dihydrate, the solution was refluxed for 15 minutes. The solvent was removed by evaporation at reduced pressure, and 50 ml. of methylene chloride was added. The insoluble water was removed by filtration. The filtrate was concentrated at reduced pressure, and subjected to column chromatography (silica gel, benzene) to give 722 mg of (3,4-methylenedioxyphenyl)acetaldehyde in a yield of 45%.

Workup

  1. temperaturethe solution was refluxed for 15 minutes
  2. customThe solvent was removed by evaporation at reduced pressure, and 50 ml
  3. additionof methylene chloride was added
  4. customThe insoluble water was removed by filtration
  5. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-b7b5e5141b8d453eb6f6e2b2edcdfd64
Source dataset
uspto-grants-1976_06
Patent number
US03962281

Reaction notes

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